Tier 2 IT Support Technician / Help Desk Lead

Massive IT; Tampa (FL); On-site; USD 75,000 - 85,000; Full time

Benefits offered by this job

401(k) matching

Dental insurance

Health insurance

Life insurance

Paid time off

Vision insurance

Job summary

Massive IT is seeking an experienced Tier 2 IT Support Technician / Help Desk Lead for our Tampa, FL office. This hands-on leadership role combines advanced technical troubleshooting with managing daily help desk operations and process improvements.

You will mentor Tier 1 staff, own escalation handling, and drive ticket management, documentation, and customer communication to ensure consistent, high-quality service.

Qualifications

• Minimum five years of professional IT support experience, including at least four years of Tier 2 IT support.
• Strong experience supporting Microsoft 365, Windows operating systems, Windows Server, Active Directory, and Entra ID.
• Solid understanding of TCP/IP, DNS, DHCP, VPNs, firewalls, and wireless networking.

Responsibilities

• Troubleshoot and resolve escalated technical support issues across Microsoft 365, Windows, servers, networks, and business applications.
• Lead daily Help Desk operations: manage ticket queues, assign priorities, monitor SLA adherence, and guide technicians.

Skills

Microsoft 365

Windows OS

Windows Server

Active Directory

Entra ID

Networking

Ticketing Systems

Leadership

Communication

Tools

PSA/Ticketing systems

Remote Monitoring Tools

IT Glue / Documentation Platform

Microsoft Intune & Azure

Job description

Date posted: October 27, 2026Company: Massive ITCompensation: $75,000–$85,000 per yearWork location: Tampa, Florida — On-Site OnlySchedule: Full-Time, Monday–FridayAbout the PositionMassive IT is looking for an experienced Tier 2 IT Support Technician / Help Desk Lead who can do more than just resolve technical issues. We need someone who can take ownership of daily Help Desk operations, provide direction to technicians, establish processes, and keep the team organized and accountable.This is a hands-on technical leadership role. You will continue working directly on Tier 2 support tickets while overseeing daily ticket assignments, technician workloads, escalations, and service delivery.We're looking for someone who recognizes what needs to be done and takes action without waiting for direction. Someone who is organized, confident making decisions, enjoys solving technical problems, and knows how to keep a busy Help Desk running efficiently.If you're an experienced Tier 2 technician who naturally takes the lead, enjoys mentoring others, and wants the authority to make meaningful operational improvements, this may be the right opportunity for you.

What You'll Be Doing

Hands-On Tier 2 Technical Support

• Troubleshoot and resolve escalated technical support issues involving Microsoft 365, Windows, servers, networks, and business applications.
• Support Microsoft 365, Exchange Online, Teams, SharePoint, OneDrive, Active Directory, and Entra ID.
• Diagnose network connectivity, DNS, DHCP, VPN, firewall, and wireless networking issues.
• Support workstations, servers, printers, endpoint devices, and related software.
• Serve as the primary escalation resource for Tier 1 technicians.
• Identify root causes of recurring technical issues and implement effective solutions.
• Maintain accurate ticket documentation, troubleshooting notes, and time entries.

Lead Daily Help Desk Operations

• Oversee the daily Help Desk ticket queue and technician workflow.
• Assign, prioritize, and redistribute tickets based on urgency, SLA requirements, and available resources.
• Monitor ticket progress and address aging, stalled, or improperly assigned tickets.
• Provide direct guidance to technicians regarding priorities, troubleshooting, and follow-up requirements.
• Ensure tickets are properly documented and customer communications are completed on time.
• Coordinate escalations and responses to urgent customer issues.
• Make day-to-day operational decisions to keep the Help Desk running efficiently.

Develop Processes & Improve Operations

• Evaluate existing Help Desk workflows and identify areas for improvement.
• Create and maintain standard operating procedures (SOPs).
• Establish consistent ticket management, escalation, documentation, and resolution processes.
• Develop troubleshooting guides and internal knowledge base documentation.
• Identify opportunities for automation and increased efficiency.
• Implement approved process improvements and ensure the team follows established procedures.

Mentor & Guide the Technical Team

• Provide daily direction and technical assistance to Tier 1 technicians.
• Reinforce expectations for ticket ownership, documentation, customer communication, and follow-through.
• Coach technicians to improve troubleshooting skills and technical independence.
• Identify training needs and assist with technician development.
• Address workflow or service delivery deficiencies directly and professionally.
• Promote accountability, teamwork, and consistent customer service.

Monitor Service Quality & Performance

• Monitor SLA compliance, ticket response times, and resolution performance.
• Identify potential service delivery issues before they become customer escalations.
• Review ticket quality, technician workloads, and recurring support issues.
• Ensure customers receive timely, professional communication.
• Provide management with updates on Help Desk performance and opportunities for improvement.

The Person Who Will Succeed in This Role

• Takes initiative: Sees a problem and addresses it without waiting to be told.
• Is highly organized: Can manage ticket queues, priorities, assignments, and follow-ups without letting things fall through the cracks.
• Leads by example: Is technically capable, approachable, and willing to help the team succeed.
• Is comfortable making decisions: Can confidently direct daily activities and resolve operational challenges.
• Values processes: Understands the importance of documentation, consistency, and established procedures.
• Takes ownership: Holds themselves accountable for their technical work and the overall effectiveness of the Help Desk.
• Communicates effectively: Can provide clear direction to technicians while maintaining professional customer relationships.

The Tier 2 IT Support Technician / Help Desk Lead is responsible for maintaining a productive, organized, accountable, and efficient Help Desk while actively contributing as an experienced Tier 2 technician. The individual is expected to take ownership of daily Help Desk operations, provide direction to the technical team, enforce established service standards, and proactively identify and resolve operational issues. The ultimate goal is to establish a Help Desk that operates consistently and effectively, develops its technicians, and delivers high-quality customer support without requiring constant management oversight.

This position requires working from our Tampa office Monday through Friday. Remote and hybrid arrangements are not available.

Benefits

• 401(k) matching
• Dental insurance
• Health insurance
• Life insurance
• Paid time off
• Vision insurance

Qualifications

• Required Qualifications
  • Minimum five years of professional IT support experience, including at least four years of Tier 2 IT support.
  • Strong experience supporting Microsoft 365, Windows operating systems, Windows Server, Active Directory, and Entra ID.
  • Solid understanding of TCP/IP, DNS, DHCP, VPNs, firewalls, and wireless networking.
  • Experience working with PSA/ticketing systems and remote monitoring tools.
  • Previous experience as a senior technician, technical lead, or escalation resource.
  • Ability to troubleshoot complex technical issues independently.
  • Experience creating or improving technical processes, procedures, or documentation.
  • Strong organizational skills with the ability to manage competing priorities.
  • Confidence providing direction to other technicians and addressing operational issues.
  • Excellent written and verbal communication skills.
  • Ability to work full-time, on-site in our Tampa office.
  • Ability to commute to Tampa, FL 33626 required.
• Preferred Qualifications
  • Experience working for a Managed Services Provider (MSP).
  • PSA and RMM experience.
  • IT Glue or similar documentation platforms.
  • Microsoft Intune and Azure administration.
  • Business-class firewall, switching, and wireless networking experience.
  • Automation experience.
  • CompTIA A+, Network+, Security+, or Microsoft certifications.
  • Familiarity with MSP service agreements and SLA requirements.
• Application Questions
  • Have you worked in a Managed Services Provider (MSP) environment?
  • Have you been responsible for assigning tickets, managing technician workloads, or overseeing daily Help Desk operations?